That Waitress in Tampa
by Velvet Sky Moon
Summary: A little story that I just had to write after a comment Dean makes in the Episode Croatoan.


I don't own Sam or Dean, or the Impala, or anything else Supernatural. The story comes from that comment in the Episode Croatoan where Sam says to Dean that 'This is the dumbest thing you've ever done'. And Dean says, 'I don't know about that. Remember that waitress in Tampa. Ewuh.' And he makes this face. I kept wondering about it. LOL What could this chick have done to make Dean react like that, and it sounded like he'd had sex with her. So, here it is. LOL

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The Winchesters were in Tampa working a fairly standard sort of haunting. Some ghost who couldn't seem to let go of the home they died in, forcing three new residents out in as many months. They were just waiting on information about if the former resident was buried or what, and where. They couldn't actually take any action tonight, and since the last resident had moved out of the house three days ago, the guys had decided that the ghost probably wasn't too big a threat. Plus, even with residents, the ghost hadn't seemed overly malicious from the reports, just kind of a nuisance, by the guys standards anyway. It hadn't killed anyone, just some injuries, one man who'd broken his leg falling off a foot stool, a woman who had gotten some bumps and bruises falling into some furniture after a scare, and a lot of frayed nerves. People seeing things moving, the water turning off or going cold or hot while in the shower or using the sink. Rattling beds, windows, slamming doors, all the stuff of a good haunted house story. So, Sam and Dean sat in a local bar having some drinks and trying to relax a little. Though Sam was still poking around his laptop and some papers while huddled in the dark, corner booth.

Dean meanwhile was leaning on the bar chatting to a chick who seemed to have had a couple before he arrived and was being very affectionate. She had on a short denim skirt and red halter top that pushed her breasts up and out a bit, which Dean had definitely noticed. She wore dark eye makeup and a deep, rich, red lipstick. She was a girl they'd met at breakfast that morning at some little diner and had slipped Dean her number. Dean had decided to take the girl's suggestion to come hang out at this little 'dive' she spent most of her evenings at. Sam had noticed that she pretty much wore the same thing at work, it wasn't the highest class place, it was basically a truck stop diner just off the interstate, frequented mostly by truckers and bikers, so her look probably got her a lot of tips. And the guy at the grill and the owner had looked not unlike the bikers and truckers. The other waitress there had been dressed similarly also. Dean couldn't really recall the chick's name now that she didn't have her name tag pinned to her shirt, though Dean kept looking at her chest where the name had been. He found though after a few drinks, it didn't matter much if he remembered names.

Sam had also noticed in the light of day that morning, that the girl seemed actually somewhat average looking in the face. There was a lot of makeup that covered up what she really looked like, though she did seem to have a nice body, so he guessed averagely attractive with a little makeup and a good body was more than enough for his brother to consider a girl 'doable'. Dean hadn't really noticed, though he'd probably only glanced at her face for a moment at a time, before his eyes settled elsewhere. Which she didn't seem to mind, and that was why Dean deemed her worth maybe going home with tonight. He had an itch and was hoping she'd scratch it for him. Dean bought her a drink, just to keep her relaxed, she was kind of petting his hand with her fingers, which felt pretty nice.

"I've been tryin' to get onto the Tampa Bay Bucs cheerleadin' squad for a couple-a years now. I mean, I'm totally a trained dancer, but there are just a lot of girls at those things. But I think I'd look so cute in one of those outfits, don't ya think?" She was smiling what was kind of a 'sexy' smile at Dean.

"Uh-huh," Dean hadn't really been listening that much to what she was saying, but he smiled and nodded with a certain degree of, what appeared to most to be, enthusiasm. He'd found with many girls before her, that usually they didn't quiz on what they said, so as long as he remembered a few bits, and then just smiled and acted interested in whatever they were saying, they were happy, and soon enough listening wasn't required. Plus he'd already figured out she wasn't the brightest bulb in the bunch, but that wasn't really a requirement for what he wanted. He kind of nodded along, figuring she wouldn't really notice that he wasn't really paying attention to what she was saying. She'd mentioned when she brought he and Sam the check this morning for breakfast that this was a cool place with good beer, which for the most part seemed true. And he'd probably remember that cheerleading bit, though the details probably weren't retained. The word cheerleader usually got some attention from him though.

She giggled a little, seeming to like that Dean seemed to agree that she'd be a great cheerleader, or that was what she got from his response anyway. In giggling though, and having had a few drinks now, she wobbled a little in her heels, and only stopped herself from perhaps really falling, by balancing against the bar. "Wow, I must be gettin' tired or somethin'." She giggled again, one might say she was a typical 'dumb blond', but from the roots showing, she probably wasn't a natural blond.

"Careful there. Maybe time to think about headin' home." Dean kind of gave her that charming grin that usually got him what he was looking for from most girls, in most bars. He was wanting some action though, and if the chick got too drunk before the 'main event,' it sucked.

"Maybe it is, but only if you're comin' home with me." She smiled, kind of coy and flirtatious.

"Now that can be arranged. Maybe I should give you a ride, I don't think you should be driving." Dean had had a few, but he was far from being drunk, just good and relaxed.

"That's prolly a good idea." She nodded and smiled, taking hold of Dean's arm. He thought it was a little goofy, but went with it.

Glancing over to the booth he caught Sam's attention and indicated from across the bar that he'd be taking off. The motel they were staying in was just a couple blocks from the bar, as luck had been, so Dean figured Sam could walk it back to the room. "Let's go then." He guided her out of the bar and to his car, oblivious to the look of annoyance Sam gave him as he left.

She ran her finger along the hood of the Impala as she made her way to the passenger's door, an action that Dean kind of cringed at, he'd just gotten the Impala washed the other day, but he bit his tongue. He wanted to get laid, and if she left any marks with her fingers, he could wash them off. She sat down, and once they were both inside the car, she shifted close, trying to kind of cuddle up as he started the car. He again, kind of cringed at that, but sometimes a few comforts had to be sacrificed for the ultimate payoff. While he was looking to get even closer than that to this girl shortly, driving was kind of a sacred thing to him, and he didn't like to be hindered by someone hanging onto him while he drove.

"So, what's with the old car anyway?" She asked, intoxicated enough she wasn't thinking with whatever brain functions she normally had. Most people would probably know not to insult a classic car like that, but there was probably some question if she'd know better even when sober.

Dean actually had to grit his teeth and half thought about pulling over and kicking this chick out right now. He whispered, almost under his breath, not really thinking if the chick next to him could hear him or not, "I'm sorry, baby, I'll make it up to ya later."

"Aw, it's alright." She smiled, having heard the soft words, thinking they were meant for her. Dean kind of rolled his eyes, the words hadn't been for her, they'd been for the car. "Oh, turn right, up here." She was fortunately aware enough to direct him to her place, which wasn't all that far. The street she had Dean turn on, just a couple blocks past the street their motel was on. Down a few blocks and she had him stop. "That's my apartment."

"Alright," Dean kind of moved to get out when she grabbed his arm.

"Wait, can we do it in here? I've always loved the back seats of big old cars." She looked kind of hopeful.

Now, it wasn't that Dean had never had sex in the Impala, but it was usually only with girls who fully appreciated the glory that was the Impala. "Let's just head in, I could go for another drink if you got one." She shrugged, nodded, and climbed out of the car.

Something was telling Dean he might want to be one more drink deep before going at it with this one. There had been a few hot girls in the bar, but she'd spotted him when he'd headed up for a second beer and had been hanging around him ever since. It kept him from being able to hit on anyone else, and kept most of the other girls from approaching. Dean always liked to keep his options open if he could. But at the time he didn't worry too much, since despite the somewhat lacking IQ, she was hot and seemed like she could be fun for the evening. Plus if he put in the time on getting a girl up to go home with him, he didn't like to not do the deal unless there was some real reason not to. And being a little dumb wasn't quite reason enough, and he was feeling pretty horny tonight. He definitely felt the need to get laid the last couple days.

She fumbled with her keys a little before unlocking apartment number 27, it was a first floor of a two story complex. Dean was kind of glad of that now, it meant he didn't have to help her up the stairs, since he figured she'd probably have been stumbling the whole way up. "Okay, home sweet home. I've got beer in the fridge." She pulled out two, not that she needed another, but she cracked one open and took a sip anyway.

It was a small apartment, the kitchen and living room kind of melded together, and he could see through the open doors into the tiny bathroom and bedroom. It appeared to be a double bed in there, and it took up a good portion of the floor space. Dean took the beer she handed him and took a long drink as soon as he opened it.

"That's such a great bar, don'tcha think? I've been hangin' out there about a year. 'Round the time I moved in here. Before that I was livin' with a roommate, this girl I knew from my last job waitressing at this bar on the other side of town. She was goin' to school and I got sick of her bitchin' about quiet and such when she was studyin'. So I finally got my own place." She was walking, slowly, toward Dean as she spoke. Stopping only when her chest was practically pushed into his. She smiled and set her beer on the counter next to them and then slid her hands up Dean's chest. He had another long drink, in those two 'drinks' from the bottle, he managed to down more than half the beer. Her hands on his chest encouraged him to shrug off his jacket and he tossed it on one of her kitchen chairs.

"Well, that sounds like it was annoying. Bet it's nice having your own place now." Dean didn't really care that much, he only paid enough attention to be able to nod and make general comments. He wasn't really interested in this girl's life, or any of that. He was interested in a good time.

"It was," Her hands still rubbing his chest, and Dean let one hand settle on her hip. She had a nice little body, everything seemed good and tight, with some subtle curves. She perhaps talked a little more than he'd like about things that he didn't care about, but he was getting by. Dean was hoping that there would be a really good payoff for this bit of annoyance. She leaned in and kissed Dean lightly.

Dean 'mmm'ed a little, now that was a good start, that was what he was looking for. When her lips pulled back he had a good drink from his beer and then set it down near by. He rubbed her sides and then let his fingers move toward getting her shirt off. He thought about saying something, but he didn't know what, and just going for it seemed the better way to go. Plus, he didn't really want to encourage her to go on any more about her bad roommates or how she couldn't seem to get onto the cheerleading squad for a pro football team.

The girl 'mmm'ed back as Dean's lips moved on hers again. Her hands rubbed his chest as he started to pull up on her shirt, which she was quite willing to loose right now. They started moving toward the bedroom as her shirt came off. Her fingers started fumbling for his shirt now, grabbing at it and tugging it off.

Dean grunted a little when the shirt interrupted the kiss. But once his shirt was discarded to the floor with hers, he went back to kissing. It was a strategy now, she was a lot hotter, and less annoying, when she didn't chatter on about things he didn't care about, so keeping her lips busy seemed a good plan. As they moved into the bedroom, Dean made quick work of her skirt and she undid his jeans and pushed them off him as soon as her skirt hit the floor. Since she lived alone, it seemed neither of them even thought to make an attempt at closing the door. It wasn't necessary.

The kiss broke a moment again, "oh yeah, take me now." She whispered before Dean covered her mouth again with his own, his tongue nudging and gaining entrance to her mouth. She seemed to 'mmm' at that moment as he also went for the hooks of her bra with one hand and expertly popped it open.

Dean pushed her down on her bed without breaking the kiss, he didn't really want to give her a chance to disturb the mood with conversation or even random comments. He was finding her voice a little grating, but so long as she was good in bed, that wouldn't really matter.

She reached to push down Dean's underwear and broke the kiss again. "Come on, daddy, get to it."

Dean was almost irritated enough to leave right now, however his 'downstairs brain' had some other ideas. He hoped if he could just get her to not speak, then they could both just have a good time. She was trim, in shape, nice breasts, though they weren't quite as large or perky as they'd appeared when her bra was still on, it apparently had had some padding and pushing factor. But still, nothing to be too disappointed about. He put a finger to her lips, his 'cool' still intact, that last beer had helped keep him from showing frustration with her less attractive qualities. "Let's not speak, it's better when the bodies do the talking." Dean smiled in that charming way and she seemed to grin back and nodded. He hoped that they could keep it to moans and groans in the vocal department. Even if she hadn't vaguely creeped him out with that 'come on, daddy' thing, Dean preferred more action and less talk, in almost all areas of his life.

Dean kissed her again, pulling off her panties as his own underwear were lost to the floor. He was glad when he didn't have to break their 'no talk' rule to ask about a condom. She paused the kiss only a few seconds to reach into a little basket she had on her bedside table and produced a condom from it. Dean smiled before resuming kissing her. He was leaned over her and between the two of them they managed to get the condom open and on him in rather quick order.

The kissing stopped again as Dean entered her, she was 'mmm'ing, "oh yeah, that's the stuff." She smiled a little, though it was a little clouded with pleasure now. Dean always loved that look on a chick, it mean he was going to get what he came for. Because if she was happy, usually he was too. He'd show her a little pleasure, and he'd get some in return, it was a good deal for everyone. He did lean in and kiss her again though, he normally didn't mind a little vocal noise during sex, but he didn't want anything coming out of this one's mouth that would kill the mood again, like that 'daddy' thing almost had for him.

The first 'round' went pretty well, Dean was feeling better now about having come home with her. He'd pretty much been in control, keeping the pace, and kissing her a lot, probably more than he did with most. Usually once the actual sex started with a chick, his lips roamed a bit, and enjoyed when the chick's did too. But he was worried about hearing 'daddy' again, so he'd kept his lips on hers most of the time. Her voice was less irritating when all she did was moan. Her moans still sounded good. He decided to take a shot at some further pleasure, since the first round hadn't worn either of them out, and hadn't quite satisfied his 'itch' completely. He risked moving his lips off hers to see about other ways to have some fun. He'd been so focused before on getting her quiet and naked that he hadn't really stopped to pay much attention to her breasts, which was something Dean usually took at least a little time to enjoy. He liked breasts, they were fun, and most girls seemed to enjoy a little attention paid to them, so it was another of those win-win situations.

So far, so good, she was 'mmm'ing and moaning softly as his lips and hands sucked and massaged her breasts. Then she said something, "mmm, yeah baby." That was okay, Dean could handle being called 'baby'. He flicked his tongue at her nipple and gave about even attention to each breast before moving south. Dean really didn't mind giving oral, though he did kind of expect if he did, he'd get the same in return.

He didn't want to encourage conversation, but he wanted to know he'd get a little return, "will you repay me on this later?" His lips had just moved south of her belly button, his intent seemed clear enough.

"I would have anyway, baby." She nodded and smiled a little, though that pleasure look was already coming back to her features, after having relaxed once they'd both come during sex. Dean had a feeling when he started kissing down her stomach, she'd gotten excited again, anticipating a little oral action.

From the way she'd come, Dean would figure he'd hit just the right spot, she seemed pretty happy, and nothing 'troubling' had come out of her mouth during the course of it. He rolled over next to her, his fingers brushing a little over her breast. She smiled, and there was a little bit of a playful, devious quality to it, which Dean usually enjoyed. It usually meant he'd end up getting spun in the best possible way.

"Hope you're ready for a wild ride, mister." She giggled pushing up a little and tossing her leg over Dean's hips, kind of like she was mounting a horse, there was something kind of hot about that to Dean. He'd almost forgotten all about his earlier worries about her tendency to talk too much and that 'daddy' reference. She leaned in and kissed him and then her lips moved down his jaw and neck, her tongue flicking out here and there. He didn't mind a little tongue on skin, though his earlobe did get perhaps a little 'wetter' than he'd have really liked. But he was anticipating a nice blow job now, so it didn't really stick long in his head.

She sucked a little on his nipples once she got to them, which Dean rather liked. Some chicks just kissed over them and otherwise ignored them. As if guys didn't enjoy a little attention there too. It was still skin that had some sensitivity, it felt good when a girl paid the right attention there.

"Ow!" Dean's blissful state of mind was rather rudely disturbed though when her teeth made a little appearance on his left nipple. His hand moved from her side to cover himself. It had really hurt, it wasn't just a little soft nip, it was a bite. "What the hell? I didn't bite yours." Dean had sat up a little, finding himself frustrated, he was still 'itching', but he also really didn't like that. What in the hell made someone think that would feel good, unless she was just a sadist or something.

"Aw, it was just a little love bite. I'm sorry." She put on this little pouty, 'I'm sorry' face, "I promise not to do it again, just lay back down. Guess we won't get that wild." She giggled a little, which Dean wasn't sure he appreciated. Though he did lay back again, albeit a little cautiously.

She moved down his body, kissing and licking, again, getting his belly button a little 'wetter' than he'd have liked. He just hoped he could enjoy this, and that she gave a good blow job so he could leave when she was done and go to bed feeling 'satisfied', despite the irritation.

Dean did come, though it definitely could have been better. He wasn't as relaxed as he should have been, though he'd relaxed a bit over how he'd felt right after she bit him. He'd had some mind blowing blow jobs, but this wasn't one of them. It wasn't bad, it was still satisfying enough, but Dean was definitely feeling like maybe he'd do best to head out while he felt like he'd at least gotten a little more satisfaction than irritation.

"Thanks, this was fun." It was at least somewhat true, parts of it had been fun. Dean started to sit up while she was still straddling his hips. "But I should head back, gotta get some sleep, got places to be tomorrow." He sort of did, but it wasn't like he had a schedule to keep, but she didn't need to know that.

"Aw, come on, baby, you're not just gonna leave me wanting more. Don't tell me you're already worn out." There was a subtle challenge in her voice. "I thought I was dealing with a man here, not just a big boy."

Dean hated being questioned like that. If a guy had said something like that to him, he'd have punched the guy. But Dean didn't hit girls, at least not unless they were possessed by something supernatural and attacked him first. But unfortunately this chick didn't seem to be possessed, she was just apparently dumb, and a bit of a bitch. To which he kind of pushed her off. He grabbed a new condom, "fine, you want more, I'll give you more." She giggled again, which wasn't cute anymore, it just kind of irritated him. One hard, fast fuck, he'd make sure he wore her out and then he'd leave. Maybe it was immature, maybe it was showing him more insecure to do it this way, but Dean didn't really stop to think about it. And if he had, it was doubtful that this chick was smart enough to think that deep on anything.

She'd gotten on her hands and knees and Dean entered her, 'doggy style'. He was running on more frustration at this point than actual sexual want. Though he relaxed a little after a little thrusting. She was moaning again and there was just something Dean found really enjoyable about being inside a girl, it was exciting, and yet managed to ease his tensions.

"Oh yeah, harder, daddy." She cried out, her body rocking with Dean's. He cringed again at that 'daddy' thing. There was just something about that, it was a turn off. But he kept going, his hands moving from her hips to the head board, for more leverage, and thrust a little harder. "Oh yes! That's it, daddy!"

Dean pushed harder, hoping if he could just get her so spun, she'd cease to be able to speak words. She shouted once more before she did seem to just fall into a series of moaning sounds. Once she did, Dean was able to loose himself a little in his own sensations. He could actually enjoy the sex, which was his main objective of the whole night, some sex he could enjoy. She seemed to come, which triggered his own orgasm. When Dean finished and opened his eyes, pulling out of her at the same. He was ready to go, he even shifted to step off the bed when he pulled out, when he felt metal on his wrist, jerking him back.

"What the hell?" He looked to see she'd handcuffed one wrist to one of the beams of the head board.

"Now you didn't think I wasn't going to get to be in control a little too. Cause we're not done yet, baby. I still want you some more. I could do this forever, actually. You're that hot, and that good." She smiled, pushing him to sit as she straddled him again.

"You might want to let a guy know first before you go handcuffing him. I mean, I didn't say I was okay with this." Dean tugged and indicated the cuff on his hand. He gave it a jiggle, he'd played with cuffs before, usually there was an easy release on them. And he growled when he couldn't seem to pop it open, then looked at her grinning at him when he couldn't get it open. "Are these real cuffs?"

"Of course, my dad was a cop." She giggled a little, when he looked irritated. "Don't worry, baby, this'll be fun. Then I'll let you out, if you promise not to run away on me. Because I was under the impression, we had all night."

Dean had never said anything to this chick about 'all night', but after a sigh, he was going to attempt the path of least resistance. Play nice, at least until he wasn't hand cuffed to the bed anymore. "Okay, let's get to it then." He grabbed her head with his free hand and pulled her in and kissed her, hard, rough, and long.

From there, she did manage to work him up again, and she took him, girl on top, and did actually ride him a little like a wild horse. When she said 'daddy' again, Dean grabbed her head again and kissed her. It just killed any mood he managed to get himself into when she said that. It seemed like it went a while before they both came, and Dean actually was feeling a little worn out when she collapsed on top of him, breathing hard, with this almost dazed smile on her face.

"See, now wasn't that worth it, baby?" She 'mmm'ed then and seemed to relax, like she was going to fall asleep on him.

"Yeah, I suppose," Dean paused a moment, the fatigue was slowing him down. He still wanted to get out of here though. For as much as he'd had some fun, he was definitely thinking it wasn't worth the irritation. There had been at least a half dozen girls at that bar who were as hot or hotter than this chick, and most probably would have been just as good in bed, without the trouble. "Now, about the cuffs?"

"In the drawer, but let's just relax a minute. I mean, what's the rush?" She seemed to want to cuddle, which Dean didn't hate perhaps as much as some guys seemed to, with a girl he was really into, he kind of enjoyed laying back after and holding her close, like with Cassie, and a few other girls who'd made an impression on him. But it really wasn't his thing. And he tended to avoid it with most 'one nighters'. It wasn't what most of them looked for, or expected in a night like this, and it definitely wasn't what he was looking for.

Dean struggled right now for the mental power to make himself push her off and find that key. But he was having trouble getting up that energy, and before he knew it, he'd fallen asleep.

Dean woke up the next morning and went to rub his eyes a little when his right arm was jerked a little awkwardly in the action. He sat up quickly and the night before came back to him, and he was suddenly aware of the music that was blaring through the small apartment, Britney Spears music. It was coming from the living room, the door still open, though he couldn't see her in the line of sight from the bed. Dean grimaced, waking up to '... Baby One More Time' was not helping his feeling better about the night before. He then moved fast, reaching for that drawer and finding the handcuff key, and releasing himself. He dressed quick, hoping to be able to just go straight for the front door. He kind of needed to use the bathroom, but not so badly that he wasn't willing to just hold it till he made it back to the motel. Dean pulled on his underwear, pants, socks and shoes, all of which were strewn over her bedroom floor. He then spotted his shirt in the living room, and her, he still couldn't recall her name, in her panties and a baby tee in the kitchen, her back to bedroom, dancing and singing '... Baby One More Time'. For a moment Dean though she looked hot, and then his 'upstairs brain' seemed to give him a mental slap and he shuddered a little and cringed.

Shaking his head Dean made sure his wallet was still in his jeans. He just hoped his jacket, with his keys in the pocket, were still on her kitchen chair, and that she wouldn't try handcuffing him to anything else before he could get out. After a breath, he went for it, grabbing up his shirt and making another face at the music as he pulled it on.

"Hey there, what's will the fully dressed. Breakfast only requires underwear." She giggled, still dancing around a little. Then she sung another few lines at the end of the song.

Dean looked relieved when the song ended, only to find the next song starting was 'Oops, I did it Again'. He visibly cringed as he noticed his jacket and grabbed it up. "Sorry, can't stay, got some things I have to do. But thanks." Dean always tried to be polite in his exit, thank a girl for a good time. Though he was less thankful for the good time, and more thankful that it seemed freedom was only moments away, and he'd never, ever, have to see this chick again.

"What? Don't like Britney?" She was pouting a little, "well, if you're busy this morning, I'll just meet up with you tonight at the bar then." She kissed his cheek.

"No, can't say I'm a fan. I used to say she was hot anyway, but she's gone a little too whack job for my tastes. I like classic rock." Dean shook his head again, wondering why the hell he was still standing here talking about Britney Spears, and not already in his car driving away. "I'm gonna be busy, so I can't be sure I'll be by. But maybe."

"But this is classic. It's before she went mental." She seemed to protest, hands on her hips.

He just needed to get out of here, now, "bye." He then made quickly for the door as he pulled his keys out. Making sure they were there, so he could, in fact, make his escape.

Dean found himself checking his rear view, often, as he drove to the motel, glad he'd never said exactly what motel he was staying at. He really didn't need this girl tracking him down. She kind of seemed like she could turn into a stalker at any moment, or maybe he just wanted to never see her again that much, that he was afraid of having to run into her.

Dean entered the motel room, about ten minutes after leaving that chick's apartment. When he got inside and closed the door, he almost fell back on the door and looked like he'd just evaded the cops or something.

Sam was sitting checking some websites and having a cup of coffee. He looked up when Dean came in and gave him a weird look. "Um, you alright?" He was kind of smirking, there was something that told him that this girl hadn't been quite what Dean expected, just from how his brother entered the room. And it was all he could do to keep from chuckling right now.

"I don't want to talk about it. I gotta take a leak. And I think I need a shower." Dean made a face, shuddering again, and then hurried off to the bathroom without another word. When the bathroom door closed, Sam laughed.


End file.
